1,2-O-异亚丙基-alpha-D-呋喃木糖合成路线 （共 87 条）
反应条件
1: 78 percent / pyridine / 0.5 h / Ambient temperature
2: 65 percent / pyridinium chlorochromate / benzene / 6 h / Heating
3: 85 percent / NaBH4 / H2O; ethanol / 4 h / Ambient temperature
4: pyridine / 1 h / Ambient temperature
5: pyridine, 80percent aq. hydrazine / 60 h / Ambient temperature
6: 82 percent / 4-(dimethylamino)pyridine, diethylaminosulfur trifluoride / CH2Cl2 / 18 h / -10 - 20 °C
7: 47 percent / CH3COOH, H2SO4
8: 1.) bis(trimethylsilyl)acetamide, 2.) trimethylsilyl triflate, 3.) 80percent aq. NH2NH2
9: 61 percent / NH3 / methanol / 48 h / Ambient temperature
View Scheme
参考文献
Gosselin; Puech; Genu-Dellac; Imbach
Carbohydrate Research, 1993 , vol. 249, # 1 p. 1 - 17
反应条件
1: 60 percent / imidazole / pentane / 3 h / Ambient temperature
2: pyridine / CH2Cl2 / 0.25 h / -10 °C
3: 56 percent / NaN3 / pyridine / 120 h / Ambient temperature
4: 95 percent / TBAF / tetrahydrofuran / 2 h / Ambient temperature
5: 88 percent / pyridine / 5 h / Ambient temperature
6: 1,) conc. H2SO4, 2.) pyridine, DMAP / 1.) 4 deg C, 6 d, 2.) room temperature, overnight
7: 1.) MSTFA, 2.) TMS-OTf / 1.) DCE, reflux, 30 min, 2.) DCE, 80 deg C, overnight
8: 52 percent / NH3 / tetrahydrofuran / 60 °C
9: 97 percent / H2 / Pd/C / ethanol / 6 h / 760 Torr
View Scheme
参考文献
Botta, Oliver; Moyroud, Elisabeth; Lobato, Cinta; Strazewski, Peter
Tetrahedron, 1998 , vol. 54, # 44 p. 13529 - 13546
反应条件
1: 66 percent / pyridine / 1 h / 0 °C
2: DMAP / acetonitrile / 2 h / Ambient temperature
3: 72 percent / AIBN, Bu3SnH / toluene / 6 h / 80 °C
4: HCOOH / 2 h / 50 °C
5: pyridine / 2 h / Ambient temperature
6: 1.) hexamethyldisilazane, (NH4)2SO4, 2.) trimethylsilyl triflate / 1.) reflux, 1,2-dichloroethane, RT, 1.5 h
7: 72 percent / NaOEt / 24 h / Ambient temperature
View Scheme
参考文献
Rhie; Pfleiderer
Nucleosides and Nucleotides, 1994 , vol. 13, # 6-7 p. 1425 - 1452
反应条件
1: pyridine; chloroform
2: pyridine
View Scheme
参考文献
Anderson et al.
Journal of the American Chemical Society, 1958 , vol. 80, p. 5247,5250
Show Details
Haworth et al.
Recueil des Travaux Chimiques des Pays-Bas, 1938 , vol. 57, p. 541,547
反应条件
2,4,6-trimethyl-pyridine in dichloromethane
T=-78°C;
参考文献
Ishihara, Kazuaki; Kurihara, Hideki; Yamamoto, Hisashi
Journal of Organic Chemistry, 1993 , vol. 58, # 15 p. 3791 - 3793
反应条件
N-ethyl-N,N-diisopropylamine in dichloromethane
T=-78°C;
参考文献
Ishihara, Kazuaki; Kurihara, Hideki; Yamamoto, Hisashi
Journal of Organic Chemistry, 1993 , vol. 58, # 15 p. 3791 - 3793
参考文献
Mota, Antonio J.; Robles, Rafael; De Cienfuegos, Luis Alvarez; Lamenca, Alberto
Tetrahedron Letters, 2004 , vol. 45, # 17 p. 3349 - 3353
反应条件
aluminum oxide
T=60 - 65°C; 20 h;
参考文献
Rana, Surjit S.; Barlow, Joseph J.; Matta, Khushi L.
Tetrahedron Letters, 1981 , vol. 22, # 50 p. 5007 - 5010
反应条件
pyridine; chloroform
参考文献
Levene; Raymond
Journal of Biological Chemistry, 1933 , vol. 102, p. 317,323
Journal of Biological Chemistry, 1934 , vol. 107, p. 75,78
反应条件
1.1: triethylamine / dichloromethane / 3 h / |Inert atmosphere
2.1: Dess-Martin periodane / dichloromethane / 20 °C / |Inert atmosphere
3.1: sodium hydride / mineral oil; tetrahydrofuran / 0.5 h / -10 °C / |Inert atmosphere
3.2: |Inert atmosphere
4.1: trifluoroacetic acid / dichloromethane; water / 0.5 h / 20 °C / |Inert atmosphere
5.1: pyridine / 3.17 h / 0 - 20 °C / |Inert atmosphere
6.1: triethylamine / dichloromethane / 1 h / 20 °C / |Inert atmosphere
7.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / |Inert atmosphere; |Reflux
8.1: trichlorophosphate / 2 h / 20 - 50 °C / |Inert atmosphere
9.1: tert-butylamine borane / dichloromethane / 0.33 h / 20 °C / |Inert atmosphere
9.2: 2 h / |Inert atmosphere; |Reflux
View Scheme
参考文献
Mandabi, Aviad; Ganin, Hadas; Krief, Pnina; Rayo, Josep; Meijler, Michael M.
Chemical Communications, 2014 , vol. 50, # 40 p. 5322 - 5325
